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US 10,476,010 B2Granted
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorGeorge Fitzgerald
Life of this patent
Estimating the term…
Abstract
Compounds comprising a ligand LA selected from the group consisting of Formula I and Formula II may be useful as blue phosphorescent materials in OLED devices. The materials were determined computationally to have appropriate triplet energies for use as blue emitters and to possess sufficient chemical stability for use in devices.
Claims17
A compound comprising a ligand LA represented by Formula I:
- wherein ring A is a 6-membered carbocyclic or heterocyclic ring;
- wherein Z is nitrogen or carbon;
- wherein R1 and R3 each represent from mono-substitution to the possible maximum number of substitution, or no substitution;
- wherein Z1, Z2, Z3, and Z4 are each independently selected from the group consisting of nitrogen and carbon;
- wherein at least one of Z1, Z2, Z3, and Z4 is nitrogen;
- wherein X is selected from the group consisting of O, S, and Se;
- wherein each R1 and R3 are independently selected from the group consisting of:
- (i) hydrogen, deuterium, halide, straight chain alkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- or
- (ii) hydrogen, deuterium, halide, isopropyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- wherein any adjacent substituents of R1 and R3 are optionally joined or fused into a ring;
- wherein the ligand LA is coordinated to Ir;
- and
- wherein the ligand LA is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand.
11 more elements
An organic light emitting device (OLED) comprising:
- an anode;
- a cathode;
- and
- an organic layer, disposed between the anode and the cathode, comprising a compound comprising a ligand LA represented by Formula I:
- wherein ring A is a 6-membered carbocyclic or heterocyclic ring;
- wherein Z is nitrogen or carbon;
- wherein R1 and R3 each represent from mono-substitution to the possible maximum number of substitution, or no substitution;
- wherein Z1, Z2, Z3, and Z4 are each independently selected from the group consisting of nitrogen and carbon;
- wherein at least one of Z1, Z2, Z3, and Z4 is nitrogen;
- wherein X is selected from the group consisting of O, S, and Se;
- wherein each R1 and R3 are independently selected from the group consisting of:
- (i) hydrogen, deuterium, halide, straight chain alkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- or
- (ii) hydrogen, deuterium, halide, isopropyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- wherein any adjacent substituents of R1 and R3 are optionally joined or fused into a ring;
- wherein the ligand LA is coordinated to Ir;
- and
- wherein the ligand LA is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand.
15 more elements
A formulation comprising a compound comprising a ligand LA represented by Formula I:
- wherein ring A is a 6-membered carbocyclic or heterocyclic ring;
- wherein Z is nitrogen or carbon;
- wherein R1 and R3 each represent from mono-substitution to the possible maximum number of substitution, or no substitution;
- wherein Z1, Z2, Z3, and Z4 are each independently selected from the group consisting of nitrogen and carbon;
- wherein at least one of Z1, Z2, Z3, and Z4 is nitrogen;
- wherein X is selected from the group consisting of O, S, and Se;
- wherein each R1 and R3 are independently selected from the group consisting of:
- (i) hydrogen, deuterium, halide, straight chain alkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- or
- (ii) hydrogen, deuterium, halide, isopropyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- wherein any adjacent substituents of R1 and R3 are optionally joined or fused into a ring;
- wherein the ligand LA is coordinated to Ir;
- and
- wherein the ligand LA is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand.
11 more elements
Dependencies are inferred from the claim text.